Dioxirane compounds have the following structure: ##STR2##
Before it was isolated or proven to exist, Montgomery 1974 and Edwards 1979 (full citations are provided below) speculated that dimethyldioxirane (DMD) was present in certain reactions they were studying. DMD was first isolated by Robert W. Murray (one of the co-inventors of the subject invention) and his coworkers, and a method for synthesizing DMD in acetone solution is described in Murray et al 1985 (full citations are provided below). DMD can be synthesized in acetone solution at relatively low cost, and stored in a conventional freezer at about 0.degree. C. for up to about a week with little or no degradation.
Various other dioxiranes have also been created, including methylethyldioxirane and diethyldioxirane (Murray 1985) and trifluoromethylmethyldioxirane (Mello et al 1988).
Dioxiranes are powerful oxidizing agents. For example, DMD has been used to oxidize primary amines, forming nitro compounds (Murray et al 1986). Eaton et al 1988 reported that dioxirane can be used to oxidize sensitive primary amines if the amine hydrochloride rather than the free amine is used. Zabrowski et al 1988 reports the use of dioxirane to oxidize substituted anilines to form nitro compounds. Prior to the subject invention, they had not been used to create hydroxylamines.